I have a problem. It’s superficial, judgmental, and immature. But it’s not going to change. I judge men by their shoes.

I think it started with my first real boyfriend. Our first date: we’re at a diner. He had on tight jeans that tapered at the ankle. My eyes continued moving down and settled on his feet. He was wearing something that seemed to hope to be sneakers but were more like slipper-sneakers. They were made of a fine, soft leather and the soles were whisper-thin. I was surprised when I recognized a famous sneaker logo. What athlete would use these, and for what sport? All I could picture was a ballerina, practicing pirouettes and leg extensions while shopping for vegetables on her day off.

“Where, um…where’d you get those sneakers?” I pretended to be absorbed in the menu, but I could feel this irritant growing within me.

He slid into the booth seat. “My mom. She works at a store where they sell designer stuff for a quarter of the cost.”

Where did this sudden preoccupation come from? What was wrong with me?

“Oh, yeah, of course,” he said sarcastically “I’m also wearing a matching bra and girdle.”

Still, he tossed the slippers out for me, and switched to more acceptable footwear. For a while. Our romance had started to fade, and then, one day, several years later, a new, even more aerodynamic version of those slippers showed up. I was moving anyway.

My very first date in New York drove all the way down from upstate for dinner. We had talked on the phone once, for five minutes. Even though several people were standing in front of the restaurant, I knew who he was immediately: he was hunched over, as if apologizing for existing. “Hi” he beamed. My eyes fell to his shoes: square toe, with a thick seam down the front middle. They were the color orange Bob Ross would use to create an Autumnal sky. Now I knew I really had a problem—not always with Homeland Security Colors –but with mens’ shoes in general.

Next was the monotone and emaciated anesthesiologist, his face so narrow it seemed like two profiles pasted together. His body ended in a pair of bloated sneakers that, instead of laces, had a thick zipper up the front of the shoe. He looked like an exclamation mark. A man should have only one zipper, and in only one place.

Then came the botanist who was always late, and whose once-lime-green ankle-high sneakers were always untied, the laces blackened with age, the ends like Rastafarian hair. These shoes really should have been thrown out before he turned 16.

Next was the dyed- platinum-blonde publicist who, on both our dates, wore shiny red cowboy boots so pointed they could have been used as toothpicks. He took a call once when we were meeting for coffee. “Sorry, I have to take this. Sooooper important?” I nodded. My eyes were drawn again to his blood-red boots. I bent close. “Oh my God, are those, like, alligator or something?” I asked, ignoring the phone call. He shook his head quickly and smiled. He covered the phone’s mouthpiece. “Armadillo!” he whispered proudly. At least I had another date that week.

That date turned out to be a man who wore cotton, Ninja-like shoes; they were split so that his big toe was separate from the others. He walked with a heel-to-toe movement so exaggerated that it was as if there were an invisible tightrope beneath him. As we were leaving the coffee house he pointed at my feet. “See, see? That’s not right. You’re not feeeeeling the ground upon which you walk.” How could a man who was essentially wearing mittens on his feet be criticizing me. Already.

So, I will keep dating – shoe-shopping, that is—until I find a supremely smart, tall, handsome guy wearing well-worn but still elegant wing-tips made of beautiful cordovan leather. Of course he will also have to forgive me for my lips rings and several nose studs. But if things go well, he and I will end the evening barefoot.

Amy Portnoy is a freelance writer, cartoonist, and illustrator. Her work has appeared in the New York Times, The Wall Street Journal, The Village Voice, andother publications.